I appreciate this article, it has told my story. One of my juniors befriended me just after I joined an organization, and one day he came with fake receipts to claim for a refund but unfortunately I think he thought he had befriended me much and there was no harm in divulging to me that the receipts were just bought at a small fee from the unscrupulous businessman, and told me that everyone in that organization was using fake receipts, but I told him to his face that since I have known that he was cheating I would not honor his claim, and on several occasions I have blocked his unbecoming behavior and that once flourishing friendship is withering down. It is somehow unsafe to befriend your boss beyond limit.
One of the first things you realize about professional life is that you’re going to be spending the majority of your time in the office—with your colleagues. And if you’re lucky, some of those colleagues will become friends.
Bonding with your peers in the office is a no-brainer, but it took a friendship with my boss early on in my career, and relationships with my staff later on, to clue me in about the complicated business of befriending your boss.
If you’re fortunate enough to have a manager that you actually want to spend time with after hours, that’s fantastic! But, before you start planning dinner parties and introducing her to your significant other, there are a few key things to consider.
What Will People Think?
You may think that your new BFF at work is your business, but the truth is, everyone from senior management to the admin staff will notice your relationship—and they’ll have an opinion about it. Make just one mistake, or even get that promotion you’ve worked so hard for, and the water cooler conspiracy talk begins.
Take a lesson I learned in one of my first positions as an example. I enjoyed my job, did well my first few years, and was even promoted. Over time, I developed a friendship with my boss (one of the few other women in our office) as we navigated the murky waters of the boys’ club together. Although my success was in no way tied to my friendship with my boss, the guys I worked with often teased me about being the boss’ “favorite.”
It was all in good fun, until it was announced our team was being phased out, and that everyone was being laid off. Everyone, that is, except for me.
Those good-natured jabs quickly turned into bitter accusations of favoritism. While I’m sure people would’ve been upset that I was the only one left standing regardless, had I not been friends with my boss, the fallout would’ve been much less painful for everyone.
No Secret is Safe
In a standard boss-employee relationship, there are some things you just don’t discuss with your boss, and vice versa. But when you become friends, that guard comes down and eventually you’ll divulge information you normally wouldn’t dream of mentioning at work. As a result, you end up arming the person who has the power to promote or fire you with your dirty little secrets.
Chances are, even if your boss has some skeletons in her closet as well, this will eventually come back to bite you—which is exactly what happened to one of my former employees several years ago. At lunch one day, I asked how she was doing. I’d noticed her performance was slipping, and she was constantly late for work. Because she felt we were friends, she confessed she’d been partying quite a bit, and even admitted to coming in to work while still a little tipsy from the night before!
Naturally, as her manager, I had an obligation to watch her like a hawk after that, which made life miserable for both of us. Understandably, the friendship ended and she eventually resigned.
While this example is a bit extreme, the point is this: Regardless of how close your friendship may be, don’t tell your boss anything that could come back to haunt you.
It’s Business, It’s Not Personal
Managers are tasked with keeping their teams running and performing at optimal levels, which requires giving constant feedback to their employees.
Hearing feedback from anyone is tough, but add a friendship into the equation and the potential for awkwardness and hurt feelings skyrockets. I’ve experienced this both as an employee and a manager, and it ain’t pretty from either side.
As an employee, I tended to waste precious time over-analyzing why my boss would’ve said “something like that to me” when I should’ve taken that time to focus on improving my work.
As a manager, I found it so much harder to coach my staff when I knew they viewed me as a friend. Knowing they could take my suggestions personally, I ended up spending a shocking amount of time coming up with ways to sugar-coat my feedback. As a result, my message was often a watered-down version of its former self, and far less effective.
Don’t Break Up With Your Boss Just Yet
After considering all these points, you may be contemplating how to end your friendship gently, or how to avoid a boss-friendship altogether.
But while this relationship is a potential minefield, it’s in no way impossible. In fact, as my career has progressed, I’ve had several friendships with my bosses, and one of my most rewarding work relationships grew out of a friendship with one of my employees.
The key to success really stems from one important skill: Can you truly separate what’s business from what’s personal? If you think you can, and you’re aware of the risks—go for it. But if you tend to overshare with your pals, or if you still feel your eyes well up when being corrected on your spreadsheet formatting, it’s probably best to keep it professional for now.